Ammonium Chloride → 2-[(2-Fluoro-4-methylphenyl)(hydroxy)methyl]cyclopropanecarbonitrile

HRID 561490Notes

Reaction equation

HRID 561490 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:5]=1[C:6]([CH:8]1[CH2:10][CH:9]1[C:11]#[N:12])=[O:7].[Cl-].[NH4+]>C(O)C.C(OCC)(=O)C>[F:3][C:4]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:5]=1[CH:6]([OH:7])[CH:8]1[CH2:10][CH:9]1[C:11]#[N:12]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 583925332-(2-Fluoro-4-methylbenzoyl)cyclopropanecarbonitrile

Product 1

HCID 583923462-[(2-Fluoro-4-methylphenyl)(hydroxy)methyl]cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

61.0 mg (1.62 mmol) of sodium borohydride were added to 300 mg (1.48 mmol) of the compound from Example 131A in 30 ml of ethanol and 13 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 1 h. The reaction mixture was added to saturated aqueous ammonium chloride solution and ethyl acetate, the phases were separated, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. 280 mg (92% of theory) of a mixture of the diastereomers of the title compound were obtained.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. addition280 mg (92% of theory) of a mixture of the diastereomers of the title compound
  7. customwere obtained

Sources & evidence

ORD record
ord-0caf49d10ea143c0bd571eef1c749fc8
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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